View 0 Caulks Field Road Chestertown, MD MLS# MDKE2003942
$9,900
Studio

Beds

0.0

Baths

0 Caulks Field Road

Chestertown, MD

Bright
Courtesy of MEREDITH FINE PROPERTIES
View Little Harbor Way # 19 Chestertown, MD MLS# MDKE2003932
  • Recently Listed
1 of 17
OPEN HOUSE: Saturday 5/4 11:00 AM - 2:00 PM
$864,000
3

Beds

2.1

Baths

1,964

Sq.Ft.

Little Harbor Way # 19

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View Little Harbor Way # 20 Chestertown, MD MLS# MDKE2003934
  • Recently Listed
1 of 17
OPEN HOUSE: Saturday 5/4 11:00 AM - 2:00 PM
$854,000
3

Beds

2.1

Baths

Little Harbor Way # 20

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 0 Colfax Road Chestertown, MD MLS# MDKE2003938
  • Recently Listed
1 of 7
$7,700
Studio

Beds

0.0

Baths

0 Colfax Road

Chestertown, MD

Bright
Courtesy of MEREDITH FINE PROPERTIES
View 1 Reed Court Chestertown, MD MLS# MDKE2003900
  • Recently Listed
1 of 30
OPEN HOUSE: Saturday 5/4 11:00 AM - 2:00 PM
$379,000
4

Beds

2.1

Baths

1,854

Sq.Ft.

1 Reed Court

Chestertown, MD

Bright
Courtesy of RE/MAX LEADING EDGE
View 128 N Queen Street Chestertown, MD MLS# MDKE2003916
$650,000
4

Beds

0.0

Baths

128 N Queen Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 7488 Poplar Avenue Chestertown, MD MLS# MDKE2003902
$250,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

7488 Poplar Avenue

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 208 Byford Drive Chestertown, MD MLS# MDKE2003778
  • Recently Listed
1 of 44
OPEN HOUSE: Saturday 5/4 11:00 AM - 2:00 PM
$385,000
3

Beds

2.1

Baths

2,045

Sq.Ft.

208 Byford Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Kinglet Road Chestertown, MD MLS# MDKE2003904
  • Recently Listed
1 of 6
$9,500
Studio

Beds

0.0

Baths

Kinglet Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View Parcel Buck Neck Ldg Road Chestertown, MD MLS# MDKE2003874
$15,000
Studio

Beds

0.0

Baths

Parcel Buck Neck Ldg Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View 214 Richard Drive Chestertown, MD MLS# MDKE2003860
$385,000
2

Beds

2.1

Baths

1,723

Sq.Ft.

214 Richard Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Sandpiper Road Chestertown, MD MLS# MDKE2003870
  • Recently Listed
1 of 2
$15,000
Studio

Beds

0.0

Baths

Sandpiper Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Buck Neck Rd Chestertown, MD MLS# MDKE2003864
  • Recently Listed
1 of 2
$12,500
Studio

Beds

0.0

Baths

Buck Neck Rd

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 23060 Old Fairlee Road Chestertown, MD MLS# MDKE2003798
$70,000
Studio

Beds

0.0

Baths

1,040

Sq.Ft.

23060 Old Fairlee Road

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 21345 Persimmon Drive Chestertown, MD MLS# MDKE2003862
$154,900
2

Beds

1.0

Baths

1,232

Sq.Ft.

21345 Persimmon Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 116 Harlan Loop Chestertown, MD MLS# MDKE2003846
$475,000
5

Beds

3.1

Baths

4,067

Sq.Ft.

116 Harlan Loop

Chestertown, MD

Bright
Courtesy of REAL ESTATE PROFESSIONALS, INC.
View 128 N Queen Street Chestertown, MD MLS# MDKE2003820
$650,000
4

Beds

0.0

Baths

128 N Queen Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 117 N Water Street N # 3B Chestertown, MD MLS# MDKE2003722
    1 of 24
    OPEN HOUSE: Saturday 5/4 1:00 PM - 3:00 PM
    $385,000
    1

    Beds

    1.0

    Baths

    652

    Sq.Ft.

    117 N Water Street N # 3B

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 117 Water Street N # 2A Chestertown, MD MLS# MDKE2003742
      1 of 25
      OPEN HOUSE: Saturday 5/4 1:00 PM - 3:00 PM
      $415,000
      2

      Beds

      1.0

      Baths

      787

      Sq.Ft.

      117 Water Street N # 2A

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 117 N Water Street # 3A Chestertown, MD MLS# MDKE2003730
      $395,000
      2

      Beds

      1.0

      Baths

      729

      Sq.Ft.

      117 N Water Street # 3A

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE

      About Chestertown

      Home of George Washington College, Chestertown is the center of amenities and the hub of life in Kent County.  Located on the banks of the Chester River, Chestertown began as a prosperous shipbuilding, trade and government center during the colonial movement and still maintains the state’s oldest records.  The popular autumn Candlelight Walking Tour offers a glimpse into many of the spectacular homes built by wealthy merchants of the 18th and 19th centuries.  Quaint red-brick sidewalks and broad, shaded streets form an idyllic backdrop for specialty shops, galleries and eateries.  On cool summer evenings, residents can relax to the strains of concerts held around the antique fountain in the town square.  Lovely homes, a stimulating college-town atmosphere and community pride make Chestertown the ideal place to call home. 

      Listings in Chestertown, MD

      87

      Estimated median home price

      $325,000
      Chestertown MD Homes for Sale & Properties

      Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

      Homes for Sale by Price in Chestertown, MD

      PriceCount
      $0 - 100K33
      $100K - 200K4
      $200K - 300K6
      $300K - 400K8
      $400K - 500K8
      $500K - 600K0
      $600K - 700K3
      $700K - 800K1
      $800K - 900K8
      $900K - 1M5
      $1M - Max11

      Homes for Sale by Type in Chestertown, MD

      Property TypeCount
      Single Family32
      Townhouse7
      Condo4
      Commercial5
      Rental13
      Lots and Land34
      Condo/Town/CoOp0
      CoOp0
      Multi Family4
      Mobile Home0
      Farms1

      (Data as of 5/4/2024)

      Information deemed reliable but not guaranteed.

      Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

      Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

      The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

      Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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